His career begins with him in charge, fronting perhaps the first of Dickerson's bands at a Chicago bar called the Entertainer's Cafe, circa 1921. He continued forming bands through the '20s, taking one of them on a 48-week tour. He hired Armstrong in 1926 for a typically extended stretch at the Sunset Cafe
--where the music began long after sunset but was sometimes still going at sunrise.
The relationship continued with Armstrong, with some substitutions in lettering on the marquee. By 1929 the band had gone on the road, and once in New York began appearing under the trumpeter's name. A 1930 job at Connie's Inn in New York City was this group's last stand under anybody's name. Dickerson's New York period concludes with some work with the Mills Blue Rhythm Band and the great King Oliver. He then returned to Chicago where he led his own bands during the subsequent two decades. His group was well known at joints such as Swingland and Rhumboogie. ~ Eugene Chadbourne, Rovi